Hydrochloric Acid → Glyphosate

HRID 462127Notes

Reaction equation

HRID 462127 reaction equation
[CH2:1]=O.[OH-].[Na+].[NH2:5][CH2:6][C:7]([OH:9])=[O:8].[P:10]([O-:15])([O:13]C)[O:11]C.Cl>O>[P:10]([CH2:1][NH:5][CH2:6][C:7]([OH:9])=[O:8])([OH:15])([OH:13])=[O:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 750GlycineHCID 14798Sodium HydroxideHCID 21884954Dimethylphosphite

Product 1

HCID 3496GlyphosateYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.6 g. of 37% formaline (= 0.1 moles of formaldehyde) are added to a stirred solution of 4.0 g. (0.1 moles) of sodium hydroxide and 7.5 g. (0.1 moles) of glycine in 40 ml. of water. After 10 minutes of stirring at 0° to 5° C, 11 g. (0.1 moles) of dimethyl phosphite are added, and stirring is continued for 2 hours at 90° to 100° C. The mixture is acidified with 60 ml. of concentrated hydrochloric acid, and stirred for further 2 hours at 90° to 100° C. The obtained solution is evaporated to dryness under reduced pressure (80 to 100 mmHg.). The oily residue is boiled with 200 ml. of 90% ethanol, the mixture is cooled, the product is filtered off, and dissolved in 30 to 35 ml. of hot water. The solution is decolorized, filtered, and the product is precipitated from the filtrate with 45 ml. of acetone. 11.0-11.3 g. (65-67%) of N-phosphonomethyl-glycine are obtained: m.p.: 224°-225° C (with decomposition).

Workup

  1. stirringstirring
  2. waitis continued for 2 hours at 90° to 100° C
  3. customThe obtained solution is evaporated to dryness under reduced pressure (80 to 100 mmHg.)
  4. temperatureof 90% ethanol, the mixture is cooled
  5. filtrationthe product is filtered off
  6. dissolutiondissolved in 30 to 35 ml
  7. filtrationfiltered
  8. customthe product is precipitated from the filtrate with 45 ml

Sources & evidence

ORD record
ord-cd785d83da724f4ca3772b9ce01f930b
Source dataset
uspto-grants-1977_12
Patent number
US04065491

Reaction notes

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